Lewis acid-catalyzed three-component condensation reactions of aldehydes, N-silylcarbamates, and allylsilane: synthesis of N-homoallylcarbamates

For simultaneous construction of the polyurethane backbone and the allyl side chains, Lewis acid-catalyzed three-component condensation reactions of carbonyl compounds, N-trimethylsilylcarbamates, and allyltrimethylsilane are studied. The reaction of these three compounds took place in the presence of a catalytic amount of TrClO4 at 0°C to yield the corresponding N-homoallylcarbamates in good yields. This reaction was also applied to the synthesis of a polyurethane having the allyl side chains.